


Secrets and skirts

by problematkit



Category: Minecraft (Video Game)
Genre: Boys in Skirts, Dead Dove: Do Not Eat, M/M, No character tags, Smut, Webcam/Video Chat Sex, angsty smut, dub con, if you found this you were looking for it, like seriously dub con
Language: English
Status: Completed
Published: 2021-01-14
Updated: 2021-01-14
Packaged: 2021-03-12 03:28:43
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 2
Words: 3,772
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28753650
Author URL: https://archiveofourown.org/users/problematkit/pseuds/problematkit
Summary: Tommy lost a bet, so he has to wear a skirt, but he's not sure he wants to. Wilbur is a little too excited for it
Relationships: Wilbur Soot/TommyInnit
Comments: 30
Kudos: 239





	1. chapter 1

**Author's Note:**

> i've been hella fixated on tombur recently.  
> I'm aware tommy is a minor  
> I am also a minor.  
> just know if you leave me hate I'll probably get off to it and it'll fuel me to write more ;)

“What, is big man Tommy’s masculinity feeling too threatened to wear a skirt?” Wilbur teased, egging the boy on.

“No! It’s just…” Tommy trailed off, excuses dying on his tongue. He looked down at the piece of clothing in his hands. A simple black skater skirt, innocent enough. It looked short though, and that made Tommy even more nervous.

“Maybe you’re not as man as I thought.” Wilbur smirked, knowing the boy would take the bait. “What a shame, I really thought you were confident.” 

He had been building up to this for months now, pushing Tommy to do more and more sexual things. He knew the kid looked up to him, knew he would do anything to impress him. He also knew Tommy would never back down from a challenge. The combination of those two things made manipulating the boy incredibly easy. Wil knew it was wrong, but he was too far gone to stop. So close to what he really wanted, he couldn’t just stop.

“Wil, I would, I really would but,” Tommy was hurt, and it showed in his voice and fidgeting hands. “If I tell you something, do you promise not to tell anyone?”

Wilbur’s breath caught in his throat at the boy’s soft tone.  _ So fucking hot. _ “Of course, Toms.” He replied, “You know you can tell me anything.”

Tommy nodded, avoiding meeting the older man’s eyes through the camera. “Wilbur it’s just that, I’m uh, I’m.” He swallowed hard, taking a deep breath. “I’m trans. I don’t think I can wear a skirt, too much dysphoria.” The words tumbled out of Tommy, and he looked at Wil’s face on his screen. “Please don’t tell anyone! And I’m still the same Tommy, please please please don’t treat me any different!” He begged before Wilbur even had time to respond to the initial confession.

“Toms! Of course I won’t tell anyone!” Wilbur had to force his voice to level out, to not betray how he really felt.  _ Jesus fucking christ, he was hot enough before, but now that I know he’s got a pussy? I have got to get him in a skirt.  _ “I’m so proud of you for telling me, you’re so brave.” He smiled kindly.

Tommy’s face lit up at the praise. “Thank you Wil, it means a lot.” 

“About the skirt thing,” Wilbur started, “I still think you should try it.” He stopped quickly, seeing the teen’s face fall. “You don’t have to, by any means! But I actually think it might help your dysphoria.” The man was careful with his next words, making sure not to let his true intentions be known. “Think about it, how amazing would it feel to know you can still be a man, even in a skirt?” He grinned, watching the gears turn in Tommy’s head as the boy considered it. “You could just put it on for a minute, not show anyone.” Wilbur suggested. “It would be really brave, I’d be very impressed.”

The last sentence sealed the deal for Tommy. “Alright, I guess.” He rose from his chair slowly, hands shaking a little. “I’ll put it on, just for a minute. No one else is home, so they won’t see me.” Tommy mumbled, the words meant only to reassure himself, but Wilbur clung to the words.

“Good boy.” The man praised, “You want me to stay on the call in case you need support?” Tommy nodded in response, and Wilbur internally exploded. While the boy was in his closet changing, Wilbur unbuckled his jeans in anticipation, hoping Tommy would show the skirt to him. 

“Wilbur?” Tommy called after a moment, “Promise you won’t make fun of me?” 

“Of course Toms!” Wilbur reassured, “I would never, I promise.” His breath hitched as the boy sheepishly reentered his webcam’s view, now wearing the skirt. 

It was indeed short, barely reaching mid thigh. The way the fabric flowed accentuated the teen’s hips. It was the hottest thing Wil had ever seen. 

“This is embarrassing, but I kinda like it.” Tommy admitted, “What do you think?” 

“You look good.” Was all Wil said.  _ If only you knew just how fucking hot you are. _ “Can you give me a spin? That’s how people show off skirts, yeah?” He asked, palming himself through his boxers.

Tommy’s face went bright red. “I would, but..” Tommy stared at the ground. “Uh, it looked weird with my boxers, so I took them off.” The boy rubbed the back of his neck. “Sorry, that’s weird, I know.” 

Wilbur felt the blood rush to his dick. “It’s not weird.” He forced his voice to sound normal. “I’m sure the skirt wasn’t really designed with boxers in mind.” The older man took a moment to plan his next words carefully. “It’s a shame I won’t be able to see the whole skirt, but I guess if you’re uncomfortable you don’t have to…” Wilbur knew the teen would take that as a challenge, he just hoped it didn’t hurt his feelings too much. 

“No no no! I can do it! I just didn’t want to make this weird.” Tommy rushed to explain, not wanting to let his idol down. “But if you don’t think it’s weird, I guess it’s okay. I trust you.” The teen gave a quick spin, before rushing to sit in his chair again. 

The quick flash of Tommy’s bare ass and pussy was too much for Wilbur to contain himself. “Oh fuck.” He groaned, pulling his throbbing cock free from his boxers, which were now wet with precum. 

“What’s wrong?” Tommy nervously asked, immediately assuming the man’s groan was that of annoyance or anger. “I’m sorry, did I do something weird?”

Wilbur chuckled at Tommy’s innocence. “No, you’re doing everything right.” The man’s mind was so clouded with lust, he was beginning to lose his composure.  _ Fuck it. _ “You’re perfect, Tommy.” His voice was low and quiet, and it hit Tommy like a truck.

“Then what was-” Tommy stopped abruptly as realization hit him. “Oh, you’re… oh.” Tommy’s eyes were wide and his mouth dropped open.  _ He’s jerking off. To me. _ Tommy knew he should think this was wrong, but something about knowing that Wilbur, his idol, thought he was hot enough to jerk off to, filled the teen with pride. “I didn’t think you would like it that much.” 

“Of course I liked it, you’re so fucking attractive, how could I not?” Wilbur practically growled, giving up on subtlety entirely. “I’ve been fantasizing about this for months, you in a skirt. Before I even knew that you were trans. That just makes it even better.” 

Tommy flushed again, “Really?” He asked breathily. He knew it shouldn’t, but this praise, the compliments, were turning him on. The teen reached his hands under the skirt, gently rubbing his clit.

“Yes, Tommy.” Wilbur breathed. “You’re fucking jailbait, you know that? You know how hard it was for me to restrain myself when you visited? Every time we were alone, all I could think about was bending you over a table and fucking you senseless.” The man smirked as he noticed Tommy’s hand under the skirt, just out of frame. “You’re liking this, huh?” Tommy nodded, unable to form words anymore. “Show me then, show me just how much you’re enjoying this.” 

Tommy tilted his webcam so his crotch was centered in frame, pulling up the skirt to clearly expose his pussy. His hand still rubbed steady circles on his clit. 

“Holy fuck Toms, you have no idea what you’re doing to me.” Wilbur moaned. “I wish I was there, wish I could fill your pretty little cunt and fuck you until you can’t remember your own name.” 

Tommy whimpered in pleasure, putting his free hand over his mouth to stifle his moans. He was embarrassed, sure the testosterone he’d been on for a year had lowered his voice, but he was sure his moans would still sound too feminine.

“Don’t” Wilbur growled, “Let me hear you. You said no one’s home, what do you have to worry about?” Tommy immediately complied with the man’s commands. “Beautiful. My beautiful little boy.” Wilbur could’ve cum to the sounds alone, “Are you a virgin, Tommy?” He asked, voice husky. 

Tommy nodded, embarrassed. “I don’t like anything touching down there, not even myself most of the time.” He struggled to speak through moans. “But I’d let you do anything you want.” He promised. 

That was all Wil needed. He came into his hand, moaning loudly. But looking back at the screen, seeing Tommy on display, just for him, was enough to make him hard again. “Well then, you’ll need to practice having something in there.” Wil angled his camera down to show the teen his cock. “I’m not exactly small.” 

Tommy’s eyes widened. “Holy fuck Wil, you’re huge.” He gasped, “You’d break me in half.” 

Wilbur chuckled, “I’d be gentle, I wouldn’t want to hurt my perfect baby.” He reassured, stroking his cock slowly. “But still, it’d be good to at least try your fingers, make it easier.” He suggested. Wil could tell the boy was hesitant, uncomfortable at the thought of fingering himself. “Do it for me?” Wilbur asked, knowing that would be enough to sway the boy. “Start with one, I’ll walk you through it, tell you how to make it feel good.” 

Tommy nodded, slowly inserting his pointer finger. It slid in easily, Tommy was the wettest he had ever been. “Now what?”

Wilbur grinned. “Now you’re gonna want to rub the roof of your pussy, like the side where your clit is, with the finger you have inside of you. Like this.” Wilbur showed the boy his pointer finger, making a “come here” motion. He chuckled as he heard Tommy’s breathing quicken. “Feels good, doesn’t it?” 

Tommy nodded quickly. He’d never felt this good before, the few times in the past he’d tried fingering himself he had felt nothing but dysphoria. But Wilbur’s reassurance and the knowledge he was making the older man happy was enough to push away the dysphoria.

“Good boy.” Wilbur softly praised, “When you’re ready, try another finger and do the same thing.” He continued stroking himself, grunting and moaning as he did.

Tommy carefully inserted another finger into himself, loudly moaning in a mixture of pain and pleasure. “It- it hurts wil” He whined, “Can I go back to one?” 

“I suppose,” Wilbur sighed, heavily exaggerating his disappointment. “But if you can’t even handle 2 fingers, I don’t think you’d be able to handle me. Such a shame”

Tommy’s face fell, desperate to not disappoint the older man. “No! I’m sorry, I’ll keep going.” He pleaded, pushing through the pain. 

Wilbur smirked, thoroughly pleased at how eager the boy was to please him. “Good boy.” He hummed, “Keep doing that, you’ll cum soon enough. After that we’ll be done for today, you’ve done so well.” 

Tommy nodded, ignoring the burning pain and just focusing on the pleasure. After a bit more of this, and plenty of praise from Wil, Tommy felt a rush of electricity as he came, squirting discharge all over his hand and computer chair. He sat panting, exhausted from what had just happened.

“Such a pretty boy, you did so well.” Wilbur came for a second time, making sure Tommy saw. “Clean yourself up, then go take a nap. You must be tired after this.” 

Tommy nodded, going to go end the call, but he hesitated. “W-wil?” He nervously asked, “Can we do this again sometime?” 

Wilbur chuckled. “Of course Toms, anytime you want.” 


	2. Chapter 2

**Summary for the Chapter:**

> Tommy and Wilbur finally meet up irl again

**Notes for the Chapter:**

> warning for some seriously dub con, like basically noncon, and manipulation. wilbur is a piece of shit in this

Tommy anxiously tapped his fingers on the windowsill of the train. It had been a few months since he and Wilbur had… had some fun over discord, and now they were finally meeting up again, alone this time. Tommy’s parents trusted Wilbur, since they’d met him before. Perhaps that was a mistake. 

Tommy jumped as the train whistle sounded, signifying it had pulled into a stop.  _ My stop _ . Tommy rose from his seat, scanning the platform for Wilbur as he exited the train. 

“Tommy!” Wilbur called the boy over, restraining himself from pulling the teen into a kiss then and there.  _ Not in public _ . “Nice to see you again!” 

Tommy beamed up at the older man. “Can we get out of this train station, asap?”

“Gladly.” Wilbur nodded.

\--

Back at Wilbur’s flat, Tommy nervously fidgeted with his shirt. “So, uh, what now? I have the skirt in my bag.” 

“Go put it on.” Wilbur ordered, “no boxers, like usual.” 

Tommy nodded and obeyed, heading to the bathroom. Wilbur’s eyes hungrily followed him the whole way.

When Tommy reemerged from the bathroom, Wil was already in his boxers, sitting on the couch. “Come here.” He growled, the softness he normally held when with Tommy gone from his voice. “On your knees.” 

Tommy silently did as he was told, confused and scared. Where was the encouraging, gentle, man he knew? 

“You’ve watched porn right?” Tommy nodded. “Good, get sucking.” Wilbur pulled down his boxers, freeing his large erection. 

The teen took a deep breath, nervously licking the tip before taking it into his mouth. His movements were slow and sloppy, clearly inexperienced. 

This continued for a minute before Wilbur sighed. “If you can’t do it right, I guess I’ll have to do it myself.” He growled, gripping the back of Tommy’s head in his hand before the boy had time to react, forcefully shoving him down. 

Tommy gagged, eyes watering in pain. He tried to push away, but Wilbur was much stronger than him. The boy struggled to breath around Wilbur’s cock, only being allowed to pull away when his face started turning blue. 

“Try again, and do better, or I’ll do that again.” Wilbur commanded. “Got it?” 

Tommy frantically nodded, taking a few gasping breaths before wrapping his lips around Wil’s cock again. He went as far down as he could handle, only getting about halfway before choking and having to pull away again to breathe. “I’m sorry,” Tommy whined, near tears, “I’m trying my best, but you’re so big and I’ve never done this before and-” 

The older man cut him off by leaning down and giving the boy a gentle kiss, trying to calm him before the kid had a full blown panic attack. “It’s okay,” Wilbur’s usual softness had returned, comforting Tommy. “Just take what you can, use your hands for the rest.” Tommy nodded. “Such a good boy.”

Tommy felt his stomach flutter at the praise, once again determined to please Wil. He took the man’s dick into his mouth again, stopping a little less than halfway down, and began bobbing his head. Like Wilbur had told him to, he stroked the remaining length with his hands. It was still sloppy, but Wilbur seemed satisfied with this. Tommy looked up at him through wet lashes, pride filling him as he saw the look of pleasure on Wil’s face.

“My pretty boy,” The man moaned, “So good, you’re so good.” His eyes rolled back into his head and he came without warning. 

Tommy pulled away, mouth and throat full of slightly bitter cum. He almost turned to spit it out, but something about Wilbur’s face told him he’d regret that. Reluctantly, the teen swallowed, and the smile Wil gave him made it immediately worth it.

“So proud of you Toms.” Wilbur praised, “Ready for more?” Tommy nodded enthusiastically and Wilbur lifted him onto the couch. “Take off your shirt, I’ll be right back.” The man walked off to his bedroom. 

Tommy shed his shirt, throwing it to the ground. He looked down at his binder, unsure if he should take it off too. He didn’t want to, but Wilbur probably wanted it off. In any case, he didn’t have time to take it off as Wilbur came back from his room with a condom and a bottle of lube. 

The man frowned as he looked down at the boy. “Take the binder off too. I want to see all of you.” He ordered, and Tommy hesitated. Wilbur could sense the hesitation, “I wasn’t asking.” He barked, “Take it off yourself or I’ll do it for you.” He grinned as the boy rushed to remove it. “Good boy, that’s more like it.”

Tommy felt overwhelming discomfort now that his chest was exposed. He wasn’t exactly flat chested. He hadn’t worn a proper bra in quite a while, but he guessed he was probably a d-cup. 

“Beautiful, such pretty tits on my boy.” Wilbur spoke softly, placing a long kiss on the boy’s lips. 

Tommy was able to ignore the dysphoria as he leaned into the kiss. He felt so loved, so cared for, there was nothing he’d rather be doing, no one he’d rather be with. His bliss was broken as the kisses moved down his neck and the older man roughly fondled the boy’s chest. Tommy squirmed, uncomfortable with the touch. “Wil, please, not there.” He whined, reaching up to pull Wilbur’s hands away. He yelped as Wil slapped his hands away.

“Shut up.” The man hissed, once again a completely different man than the Wilbur Tommy was used to. “You’ll get used to it.” 

Tommy was too afraid to protest, instead just nervously nodding. The boy tried his best to focus on the kisses and bites being placed on his neck and shoulders, but the discomfort of his chest being touched was overwhelming. 

Tommy didn’t know how long he zoned out, but he was brought back by the feeling of Wilbur’s large hands on his inner thighs. The boy realized his face was wet with tears, and he reached up with shaky hands to wipe them off. 

Wilbur looked Tommy in the eyes, sighing in annoyance. “Stop with the tears, aren’t you a big man? Can’t even handle a little bit of touching?” His voice was tinged with anger, reigniting the fear in Tommy. 

“Sorry, I’m sorry.” Tommy mumbled, trying to steady his breathing. “Maybe we should stop, I don’t know if I can do this.” His heart raced as Wilbur glared at him, “I know I promised before I got here but this is all so much,” He rambled, frantic to explain himself, “I’m really sorry, Wilbur, seriously. I’ll make it up to you another time but I can’t do this-” 

Tommy sat in shock as he was cut off by Wilbur harshly slapping him. “Shut the fuck up.” The man hissed, “I don’t give a fuck if it’s too much for you, you don’t get to get me all hard, promise me you’ll let me fuck you, and then just back out.” He grabbed the bottle of lube and the condom, holding one in each hand. “You wanna talk back, you’re getting punished. Pick one.” 

Tommy felt like he was going to throw up. This wasn’t Wilbur, Wilbur would never be this mean, Wilbur wouldn’t do this to him. His mind was racing, unable to form words. 

Wilbur grew impatient. “Fine, since you’re not choosing you get neither.” He chucked both items to the side. What Tommy didn’t know, however, was that this had been Wilbur’s plan from the start. He wanted it to hurt for Tommy, give him something to remember, and he wanted to really feel the boy.

“Wilbur, please, no!” Tommy pleaded, desperately trying to shut his legs, to push Wilbur away, anything to stop this, but it was pointless. Wilbur pulled Tommy’s legs open and stepped between them to keep them open, then grabbed both the boy’s wrists in one hand and pinned them above his head. 

“You got yourself into this. You have no one to blame but yourself.” Wilbur growled, using his free hand to line his cock up with Tommy’s entrance. “If you relax, it’ll be easier.” 

Tommy felt tears running down his cheeks once again and he turned his head to the side, trying to find something to distract him from what was happening. 

Wilbur forcefully turned the boys head back to face him. “Look at me.” He ordered, “Look at me while I completely destroy you.” The man forcefully thrust his cock into Tommy’s tight pussy, ignoring the boy’s scream of pain. He didn’t bother to wait for the kid to adjust, just repeatedly slammed into him. “You feel so good, my pretty boy.” He moaned. 

Tommy’s whole body shuddered with sobs. His eyes were puffy and red from crying and he wanted nothing more for this to end, for Wilbur to suddenly snap out of whatever he was doing and stop.

Wilbur had no intentions of stopping. The pleasure was too intense for him to even consider it. Knowing that he was absolutely destroying the teen boy below him made a grin spread across his face, cruelty in his brown eyes. He leaned down and started sucking and biting on Tommy’s chest, leaving marks all over. “You’re going to remember this forever, I’m sure of it.” He smirked.

This continued for god knows how long, Tommy slowly but surely detaching himself from the present. His mind and body went numb as he stared straight ahead. He was reminded of what was happening when the man inside him slowed his rhythm, grunts and moans growing louder.

“I’m cumming inside you.” Wilbur said, voice husky and low, “I’ll get you some plan b or something.” 

Tommy felt the tears start again as warm fluid filled him up. Wilbur pulled out of the boy, silently wiping his dick on his discarded underwear. The only noise in the flat for a few moments was gentle sobs, until Tommy built up the strength to speak. 

“W-why?” He asked, voice hoarse from crying, “Wilbur why?” 

The older man’s face softened. “I really didn’t want to, Toms.” He cooed, “But you needed to learn your lesson.” Wilbur placed a gentle kiss on Tommy’s forehead, smiling as he felt the teen melt at his touch. “I’m sorry, my pretty boy, I wouldn’t have hurt you if I didn’t have to.”

Tommy was incredibly conflicted, unsure of how to react. This was the man he knew, soft, gentle, and kind, but he had just hurt him immensely. As the man stroked his hair, Tommy knew he wouldn’t be able to stay upset at Wil.  _ It was my fault anyway. I trust him. _

“Let’s get you cleaned up.” Wilbur scooped Tommy up in his arms, carrying him like a baby towards the bathroom. “You can take a nice warm bath, and I’ll make you some tea.”

Tommy weakly smiled at the comforting words. “Thank you.” He whispered, nuzzling his face in Wilbur’s neck. 

“I love you Toms.”

“I love you too.” 

**Notes for the Chapter:**

> Thanks for reading :) I was gonna wait until tomorrow to post this but I figured, fuck it, why not. This was my first ever smut fic and my second ever fic period, so if its a little wonky that's why.

**Author's Note:**

> this had no character tags, so before you comment hate just know everyone who sees it will know you went looking for explicit tombur fics


End file.
